Tetrabutylammonium Fluoride → 1-(5-(4-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

Beteiligte Stoffe

Reaktionsschritte

The title compound was prepared from 4-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl acetate (30 mg, 0.059 mmol) following General Procedure D except the reaction with Bu4NF stirred for 5 h. Preparative thin layer chromatography (40% EtOAc) yielded the title compound as a white solid (2.4 mg, 10%): 1H NMR (CDCl3, 600 MHz) δ 7.66 (d, 2H, J=8.4 Hz), 7.37 (s, 1H), 7.27-7.25 (m, 2H), 7.17-7.16 (m, 3H), 6.91 (d, 2H, J=8.4 Hz), 3.06 (t, 2H, J=7.5 Hz), 2.60 (t, 2H, J=7.5 Hz), 1.79-1.75 (m, 2H), 1.65-1.61 (m, 2H), 1.43-1.38 (m, 4H); 13C NMR (CD3OD, 125 MHz) δ 188.7, 161.1, 159.2, 157.7, 143.1, 128.8, 128.7, 127.6, 126.0, 122.7, 120.0, 116.6, 39.3, 36.3, 31.7, 29.5, 29.4, 24.5; MALDI-FTMS m/z 350.1748 (M+H+, C22H24NO3, requires 350.1751).

Herkunft & Nachweise